Cheap Flights from San José (SJO) to Chicago (ORD)

Popular airlines from Juan Santamaria Intl. Airport (SJO) to Chicago O'Hare Intl. Airport (ORD)

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Flights from San José (SJO) to Chicago (ORD)
Origin airport
Juan Santamaría Intl.
Destination airport
O'Hare Intl.
Distance
3553 km

San José to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from San José to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from San José to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Frequently asked questions

How long does it take to fly from Juan Santamaria Intl. Airport to O'Hare Airport?
Purchase your ticket with United Airlines and you can expect to be airborne for about 5 hours and 28 minutes. This reputable airline has a direct flight that leaves at 1:00PM from Juan Santamaria Intl. Airport (SJO) and lands at ORD at 7:28PM. Expedia has some epic flight deals, so find out what's available on this route today.
Is it cheaper to buy a plane ticket from SJO to O'Hare Airport last minute?
Booking your journey from Juan Santamaria Intl. Airport to O'Hare Intl. Airport (ORD) last minute could save you a pretty penny if you're lucky to find a terrific deal. However, tickets usually don't drop in price closer to the departure date. If you wait around, flights could also be booked up or the best seats taken (we hope you like the middle seat!). If you'd rather not hedge your bets, book well in advance of your departure date. Don't forget that some of the biggest bargains can be found up to 12 months in advance. If your preferred airline hasn't released its fares yet, check back regularly as offers are updated on Expedia all the time.
What airline has the least delays from Juan Santamaria Intl. Airport to O'Hare Airport?
With an on-time performance score of 60%, United Airlines is the airline that's more likely to get you from Juan Santamaria Intl. Airport (SJO) to ORD without any delays. Flight delays aren't just irritating — they can also cause you to miss an important connection or even ruin your entire vacation. You can prepare for delays by reviewing your flight status through the free Expedia App well before you get to the airport. If you're already at your gate and you're worried about the knock-on effects, visit your airline's customer service desk to figure out your next move.
What airports do you fly into for Chicago from San José?
O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are your choices when jetting from San José to Chicago. Around 26 kilometers northwest of central Chicago, O'Hare Intl. Airport (ORD) is the city's major gateway. Consider factors such as flight arrival and departure times and the distance to your hotel before deciding where you fly into. Wrigley Field and Millennium Park are a couple of terrific attractions to put on your to-do list when you arrive at your destination.
What are the most popular departure times for flights from SJO to ORD?
For United Airlines flights heading from Juan Santamaria Intl. Airport to ORD, the most popular departure times are between 1:00 PM - 2:00 PM. If you'd like to avoid any holdups, head out in the morning. This way you're likely to avoid air traffic that builds up around airports in the afternoon.
Can I change the date of my flight from Juan Santamaria Intl. Airport (SJO) to O'Hare Airport?
We know plans can change, so Expedia is here to help make amending your flight as easy as possible. First, access your Juan Santamaria Intl. Airport to O'Hare Intl. Airport (ORD) itinerary through the Expedia Trips portal and browse the ticket conditions and rules about what changes can be made. If you booked in the last 24 hours, some carriers will let you cancel without charge and organize new flights. If you bought your fare more than 24 hours ago, get in touch with us through our Customer Service portal so we can assist you further.

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